Acetic Anhydride → HCID 13769774, compound

HRID 979948Notes

Reaction equation

HRID 979948 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]3[S:29][CH:30]=[CH:31][N:32]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:27]([C:28]3[S:29][CH:30]=[CH:31][N:32]=3)[C:33](=[O:35])[CH3:34])[CH2:23][CH2:24]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13769658HCID 13769658, compound

Product 1

HCID 13769774HCID 13769774, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.76 parts of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[2-thiazolylamino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine, 15 parts of acetic acid anhydride and 40 parts of acetic acid was stirred and refluxed overnight. The reaction mixture was evaporated and the residue was taken up in water. The whole was alkalized with ammonium hydroxide and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The second fraction was collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 4.9 parts (66.3%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-amino]-1-piperidinyl]ethyl]-N-(2-thiazolyl)acetamide; mp. 185.5°-193.0° C. (compound 102).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. extractionthe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe second fraction was collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-7fab710bbdd54089b5d22258dba3bb38
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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